What’s it like to work professionally with your ex-boyfriend’s brother? For Demi Lovato, luckily, it’s not awkward at all.

The 21-year-old is currently on her Neon Lights tour, with pal Nick Jonas as the Musical and Creative Director. Of course, four years ago, she dated his older brother and bandmate,Joe Jonas, and after they broke up she checked into rehab.

Naturally, when Demi appeared on Chelsea Lately Thursday, the funny talk show host had to make things a bit uncomfortable. “Which one’s the cute one?” Chelsea Handler asked, of the famous family.

The singer had a witty response of her own, though. “They have a new niece and she’s really, really cute,” she winked, referring to Kevin Jonas’ newborn daughter, Alena Rose. Even Chelsea had to compliment her on that one. “Great answer,” she laughed.

When asked what it’s like working with an ex’s sibling, Demi made sure to clear something up. “We dated for, like, a month!” she explained. “Everyone made it seem like it was, like, this big, big deal!”